“Antifragility is not just the opposite of fragility. A fragile object breaks under stress. A robust object stays the same. An antifragile object gets better.” Nasim Nicholas Taleb

This summer, I dove deep into the chaos of life.

Some nights I’d sleep at 10pm. Others I’d sleep at 8am. Sometimes I wouldn’t sleep at all. I used no schedule. I had no to-do list. I’d often get on calls with friends from home at 11pm or 4am. I’d write in cafes, restaurants, planes, trains, and hotel lobbies. I met witches, magicians, spiritual teachers, spiritual narcissists, healers, guides, ladyboys, lovers, and lifelong friends.

Life presented me with many challenges this summer. Stolen wallets. Infections and injuries. Negative bank account balances. I’ll dive deeper into these later in the letter.

Through the chaos and the challenges, I’ve returned home stronger, more robust, more resilient, more adept at handling problems, and above all, more antifragile. This was my summer of antifragility. I will never be the same after this adventure.

The Modern World Makes Us Fragile

We live in a society of fragile people.

Our processed diets, endless entertainment, and a plethora of vices leave us with weak jaws, weak bodies, weak minds, and weak spirits.

Our ancestors fought in wars, traveled across deserts and mountains, and hunted for food to survive. Yet it is my generation who claims victimhood at the most minor inconvenience, be it a test they “have to take” for the major they “have to study” to get the job they “have to get,” or God forbid someone misgenders them or mislabels them pronouns.

Many of these delusional youth, especially in the Western world, are living in a fantasy world akin to Peter Pan’s “Neverland,” never growing up and expecting everything to be handed to them. If it’s not, they’ll claim they are victims of bad parents, unfair teachers, the system, the patriarchy, racism, sexism, or the multitude of other “isms” you often find shouted throughout liberal arts universities in America.

I am not a pessimist, but imagine something truly catastrophic happened in the world, be it a nuclear fallout or a world war. Imagine, as our ancestors did for millions of years, we went without electricity, technology, Doordash, and Netflix and had to really fight for our lives and struggle for our survival. Who would survive? Who would thrive? Who would find a way to persist and figure things out?

The antifragile would. 

Those who are built to handle chaos. Those who are self-sufficient enough to fend for themselves. In this hypothetical “doomsday” scenario, it is those who have dropped out of and learned to live outside of the system that would have the character traits and the resiliency to persist amidst a crisis.

In the modern world, those who embrace the definition of antifragility are the entrepreneurs, the innovators, the artists, the crypto-wizards, the freelancers, the world travelers, and the out-of-the-box thinkers. To the masses, they appear as radical, adventurous risk-takers. But to those in the arena, they know there is no other way to live. The only other option is a life of complacent mediocrity, uncomfortable comfortability, and the possibility of looking back on their life on their deathbed and wondering if they ever even tried to live up to their potential.

This summer, I stretched my ability not only to survive, but thrive amidst chaos. I became comfortable achieving nothing, having nothing, and living at the edge of the unknown. I grew stronger, more resilient, and more sovereign as an individual. But it was not without challenges, uncertainty, self-doubt, and a handful of eye-opening experiences about the reality and hardships currently going on in the world.

Leaving Innocence

I grew up in a very safe place with a very comforting family in the suburbs of Illinois.

I never had to worry about eating. I never had to worry about money. I never was confronted with the dark side of the world we live in. That was only stuff I saw on the news. It never applied to me.

For this, for my parents, for my grandparents, for my community, and for my education, I am incredibly grateful. My upbringing gave me the foundation of stability and security that has allowed me to willingly leave order and security and voluntarily dive headfirst into chaos.

Similar to the Buddha voluntarily leaving his palace and witnessing the “four sights,” I have voluntarily ventured off the safe path to embark on the pathless path.

Why?

Many people ask this. I sometimes ask myself.

I could theoretically stay in America, get a top-10 degree, work a $200k finance job, and live a comfortable, abundant life. Even psychics and astrologists recommend I do this.

But no. Something in me has to go explore. It’s in my nature. I’m meant to adventure, carve my own path, and stretch as close to my highest potential as possible. Maybe it’s my Sagittarius rising. Maybe it’s my soul’s density. All I know is that I’ve left the metaphorical cave, I’ve taken the red pill, and my eyes have been opened. I cannot go back to the matrix and programmed life knowing what I know and seeing what I’ve seen.

This summer, I saw and experienced things that opened my eyes to reality outside of the comfort of suburban America, Western society, and Neverland. But it is only outside of Neverland that a boy can become a man.

I saw drug abuse. Immense amounts of lust and sexual desire. Very sad and lost people. People completely detached from reality. I was tempted by all of these.

I saw poor families barely scraping by in street markets. My good friend’s ex-girlfriend is facing life in prison for selling drugs at parties. A girl died on a hike in the town where I was living. Suffering was closer to my face than ever before. And I was only in Thailand. I can only imagine what it would be like in India or Africa. Stay tuned for that adventure.

But despite the suffering I saw, I also saw immense beauty and many people on their own journeys looking for more out of life, and finding it. My eyes were opened to infinite possibilities of how one could live their life.

I met monks, gypsies, spiritual teachers, entrepreneurs, artists, chefs, and witches. I saw how people found ways to make a living in such interesting ways, be it a traveling DJ career, selling crystals at street markets, doing Tarot readings at parties, working remote jobs from 10pm-4am, or starting their own coffee shop or coworking spot across the world.

These people were living outside of the script society assigned to them. They were writing their own scripts. Living their own surrender experiments. At home, every single one of my friends is either working a 9-5 job or trying to find one. It’s often difficult to connect on this level or have the typical “what do you do for work” conversation that dominates family events, dinner parties, or the bar scene because I’m living so outside of any conventional box. I’ve learned to navigate these with grace and move beyond judgment. But it was beautiful, empowering, and reassuring to meet so many souls who also decided to opt out of the game and embark on their own adventures and realize I wasn’t alone on this quest.

Thriving Outside of Structure

From as early as I can remember, up until this summer, I lived within the structure of strong, focused masculine energy, but always craved more spontaneity and feminity.

As a kid playing football and basketball, I did well within the systems and schemes the coaches defined for us, but I was always best off-script, out of the pocket, or on the fastbreak, creating and trusting my intuition.

College football and an economics major required immense discipline and a defined daily routine to succeed. Starting my own business in the creator economy brought with it constructing systems, steadfast determination, and unwavering focus.

I was good at what I did. In college, I was on track to a high-paying finance career, and in the creator economy, I saw success early. But in the depths of my soul, I was always craving something different, something more novel, and something more adventurous.

A big reason I went on this adventure this summer, although it was mostly unconsciously, is I wanted to get back to playing “outside of the pocket” and “running the fastbreak.” I desired spontaneity, femininity, and surrender.

This chaos I craved was exactly what I got, and I became stronger as a result. This summer marked an internal shift from Prince energy to King energy. But for a Prince to become a King, he must slay some dragons along the way. I faced many dragons this summer.

Slaying Dragons

“Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors… Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.” Nasim Nicholas Taleb

If you read my recent blog, you remember I mentioned how the book Badulina made a significant impact on my perspective and worldview.

An idea presented in this book was that every King can only be a King if he slays dragons along the way. "Dragons" can be looked at as problems, roadblocks, or inconveniences in anyone's life.

In the story, the narrator is tasked with fixing the drainage system in his sink. Instantly, he wants to call a plumber and says, "I can't fix sinks."

The King proceeds to tell him a story about the greatest dragon he ever slayed, a situation where he was stranded in the 140-degree desert with 1/16 a gallon of gas and a flat tire and had no choice but to figure it out.

As he tells the story, the narrator begins to work on the sink. In the climax of the story, when the King miraculously changes the tire, escapes the desert, saves his life, and explains how he reached a new level of power and truly became a King by slaying his dragon, the narrator unclogs the drain and reaches a new level of self-empowerment and belief that he can solve any problem life presents to him.

The moral of this story is that life will always present us with dragons to slay. We can either shy away from them, play the victim, and shrink in the face of discomfort, or we can rise to meet the challenge, step into our King-like power, become more antifragile, and solve any problem life may present to us.

"When you're good at solving problems, God gives you lots of them." ~ Patricia Sun

This summer, life presented me with a handful of dragons, each one prompting immense doubt and fear within me, but on the other side, led to greater levels of confidence, empowerment, self-belief, and King energy.

My Dragons

On the surface, tons of things went wrong this summer.

When I tell my parents about some of these experiences, they nearly have a heart attack. But I always reassure them all is well and always had been well, even when I couldn’t see it, and that everything was unfolding perfectly in the grand scheme of things and from the perspective of the universe. This probably does little to comfort them, but it is a knowingness and trust that exists in the depths of my being.

Over the course of the three months, my computer broke from water spilling on it, my iPad stopped charging because sand got inside the charging port, my iPhone stopped charging for reasons I still don’t know, and my AirPods fell in a puddle in the middle of a rainstorm.

For a few days, I had no devices. But I was always able to figure it out. I found a Mac repair shop in the middle of a farm a mile deep on a dirt trail in the middle of nowhere to fix my computer. I ordered a wireless charger from Lazada (Thailand’s Amazon equivalent), and it arrived in perfect timing. My Airpods and iPad miraculously started working the moment I accepted they’d be broken forever.

I got staff infection from the climate, mosquitos, sleeping in dorm room beds, poor personal hygiene, and continuing to go dancing at parties despite my body telling me not to. A friend referred me to an incredible pharmacist with ointment to cure the infection, and another friend, an ex-Israeli military medical expert, treated an infection on my toe.

I got a rock stuck in my heel (twice) from running around barefoot and dancing at parties without shoes. I got it surgically removed from an incredible doctor (shoutout to Dr. Terry) at a medical clinic for about $20. The lesson here was to slow the f*ck down, and the rock in my heel was the universe reminding me my Achilles heel has always been rushing.

Then, my wallet was stolen at a party in the South of Thailand, and I was left with no credit cards, no debit cards, and no way to pull out money. Thankfully, my friend Milana was able to give me 20,000 baht (about $600 worth) to use throughout my two weeks of traveling back north to Pai. In Pai, at the brink of running out of cash, I was eating pizza and sipping wine when I realized I had $3 cash left. Yes, $3.

In divine timing, my friend Heather (who I lent money to two months prior) pulled around the corner to hand me another 15,000 baht to last me my last 10 days in Thailand. When I told her it was perfect timing because I had $3 left, she said, “Omg, how were you not freaking out?” 

My response was crystal clear:

“I have faith in God.”

Money troubles came up again a week later. I had $1025 cash liquid in my bank, and most of my money was in Coinbase. I was having a massive internal shift at this time, with clarity on Conscious Creators and other programs coming forth, had just fallen down Nicky Ortega’s rabbit hole, and intuitively felt I was supposed to invest $999 in her Skool community. I documented my emotional state and how I navigated the entire experience in a video that I’m putting inside of Conscious Creators called “Making a Quantum Leap in Real Time.”

After I paid her the $999 and had $26 in my bank account, I was waiting for $4500 to transfer from Coinbase. Here’s where everything got fucked up.

I had an automatic $250 per week transfer from my bank to Coinbase set up to reoccur every week. However, I had $26 in my bank account, so when the auto-transfer tried to push the day after, my bank account went to -$224, and Coinbase froze my account, so I couldn’t pull money out of Coinbase and back to my bank to use. Essentially, all of my money was in Coinbase, but I couldn’t access it because my account was frozen.

To make matters worse, the $4500 I tried to transfer to my current bank somehow got sent to an old, closed savings account I couldn’t access or reopen. To this day, 2 months later, this $4500 is still floating in space, between banks, with Coinbase reassuring me “their team is looking deeper into this case.” Bullshit. Lol.

Luckily, the next day, $300 hit my bank account from recurring sales from my old Internet Freedom course. Now I had enough money to complete the auto-transfer to Coinbase, reactivate my account, and pull the $7000 I had remaining back into my bank.

As always, everything was happening in divine timing, but fear tried its best to take hold of me. For about a week, I had literally no money to access. I was living off the $500 cash I had just received from Heather. Right when I needed it, the money always magically came, just like it always had, and just like it always will.

“The universe whispers until it screams.” ~ Brianna Weist

When I wasn’t listening, the universe would scream at me in the form of a problem or injury.

I believe each of these dragons also contained a golden lesson hidden beneath it. My devices stopped working because I wasn’t engaged in the present moment enough. My Airpod fell in a puddle because I was overloading my dopamine system with music. My infections were a sign I wasn’t taking proper care of myself. The rock in my heel was a sign to slow down. My wallet getting stolen was both a lesson to not be too trusting, but also to trust that God and people would always be there to support me if I ever went without money.

The money issues with Coinbase and my bank were also a blessing because the situation began to shift my focus from total surrender and the spiritual path to coming back to business. I hadn’t made a dollar for three months that summer, other than some recurring payments from a previous asynchronous course. Now that money became a new dragon, my subconscious began to go to work on it and develop ideas on how to make immediate cash flow in the short term while still maintaining the long-term visions of retreats, festivals, books, and the school.

As I’ve returned home and shifted my attention to scaling my income again, and with reinvesting this income into the bigger visions as the purpose, an idea for a new 1v1 consulting offer and different coaching calls came to me. Within a week of “launching” this offer and these calls, I made $20k.

All of these obstacles made me more antifragile. I wouldn’t have unlocked this clarity for my new offer without the dragon life presented to me. For this dragon, and all of my dragons this summer, I am incredibly grateful.

“The ultimate aim is not to eliminate randomness and uncertainty, but to harness them and use them to fuel improvement, learning, and adaptation.” ~ Nasim Nicholas Taleb

Partying > Celebrations of Life

I’ve highlighted many of the obstacles and challenges life presented to me this summer. But these were just a paragraph in the larger story of this adventure.

The most magical part of this summer was unplanned and unintended, like most magical things are. My intentions going into this journey were to meditate, practice yoga, and deepen my spirituality. But the spiritual experience my soul really needed was going to parties and having so much fun. Or, as I am reframing them, celebrations of life.

Maybe the most magical party I went to this summer was a party called “Eden” in Koh Phangan. To get there, you have to find the departure point on a beach and take a 15-minute row boat across the sea to another island where the party is hosted. The party goes all the way until the next night, so I decided to sleep for a bit and woke up at 430am to drive my motorbike across the island to find the departure point.

I got there at around 530, and our boat left for the party right as the sun was rising. Never in my life had I woken up at the crack of dawn to go on a rowboat to a hidden party on an island, but I could expect nothing less this summer.

Right after getting there, I put my wallet down next to my shoes in a spot I thought was secretive so I could go dance, but within 15 minutes, it was gone. Another dragon. I realized I had the choice to be upset, or I could choose to still enjoy myself, knowing there was nothing I could immediately do other than go on my phone and freeze my credit cards. I decided to have a good time.

At one point in this party, I looked around and saw everyone as children. I saw how everyone is just a grown-up kid who wants to have fun. Instead of seeing the scene as a party, I saw it as a celebration of life. Instead of seeing everyone escaping reality (though of course, there is always some of this), I saw everyone immersing themselves in it. I’d gone into these travels judging partygoers and ravers. But after allowing myself to experience it, I fell in love with the scene, and realized I wanted to bring more celebrations of life into the world.

Clarity came for a vision for wanting to host festivals around the world. I realized I experienced just as much, if not more, expansion, freedom, and love from these parties as I did from a medicine journey, a meditation session, or reading a spiritual text. A project I want to bring to fruition in the next few years, maybe in 2025, is to throw a festival (or a few) around the world featuring breathwork, meditation, guest speakers, incredible food, beautiful scenery, ecstatic dances, medicine journeys, and raves. It’s all a part of the human experience.

I realized how important parties are for the human spirit. They are celebrations of life. They are just as “spiritual” as going to a yoga retreat or doing vipassana if your eyes are clear enough to see. You can experience as much freedom from a rave as you can from a mushroom journey.

The spirit of God is equally infused in a rave as it is in a group meditation. Creating a duality between the two, or labeling one as good and one as bad, prevents you from seeing God in all. If an ounce of judgment exists, you’ve lost clear-sightedness and fallen into the duality of the ego. When you see everything as God's creation or God in action, the rave is just as spiritual as an ayahuasca retreat or reading the Bible.

Learning From DJ's

At these celebrations of life, I fell in love with psytrance music. I learned about myself through the music, and I learned about life and people through the crowd and the DJs.

The best DJs know that what matters is if the crowd is having a good time and that they are the vessel for creating the vibe of the party, but it’s ultimately not about them. They have an intuitive feel for what the people want, and they have the skill and artistry to give it to them. These DJs are like magicians in the way they can control the mood of the rave by choosing the right song, frequency, and beat at the right time.

“A DJ is there not just to play records, but to interact with the crowd. It's almost like we're magicians. We have to feel what the crowd wants, anticipate it, and then guide them somewhere they didn't expect to go. It's an art, and when done right, it's pure magic.” ~ Carl Cox

My favorite quote this summer came from a friend and DJ in Pai named Love. He was most definitely living in the spiritual paradigm and above the level of love on the Hawkins Scale. I asked him how he knew when to play which song, and his answer was beautiful.

“It is not me who is playing the music or choosing the song. I am a channel for the universe. The universe speaks through me in the form of music. I’m not doing anything.”

Looking back, this quote likely planted a seed to change my social media bio across platforms to “A vessel for God’s creation” and formed the foundation of my ethos for building Conscious Creators, retreats, festivals, and writing books. The paradox is that they are “mine” because “I’m” creating them, but the reality is I am merely a vessel for allowing the collective consciousness to channel through me in the forms of these creations.

As Love said,

“It is not me who is playing the music.”

The Summer of Antifragility

I call my adventure over the last three months “The Summer of Antifragility” because I realized not only do I not need the perfect routine, systems, and structure to thrive, but I can thrive in chaos.

I tapped into new levels of creativity at 3am at raves. I met unique souls on unique journeys I never would have met at home. I learned to navigate obstacles and slay dragons I never would have experienced inside a tightly defined routine. I opened my heart, got my heart broken, and experienced love for the first time in years. I surrendered to life, stepped away from achieving, became comfortable being nobody, and came back full circle to my vision and mission from a new place internally.

Before I left for Thailand, I had the intuitive sense that if I stepped away from the games I was playing, I would be able to zoom out and see the playing field from a new perspective. I’ve returned with a newfound sense of both clarity and motivation for the projects I want to build and my mission of actualizing human potential, but also a lightheartedness and playfulness about them I was never able to access before. This new internal place is allowing me to think and dream bigger than would have been possible had I not gone on this adventure.

The next chapter of my life is one I feel will be full of rapid action, progress, and expansion of manifesting my visions into reality. But it will come from a new place. One of play. Of peace. Of love. Of lightness.

And even as I enter a new chapter, one that will bring with it more focus, discipline, and building, I will never forget the playfulness and surrender experiment I experienced this summer.

Thank you Thailand.

You will hold a place in my heart forever.

<3

Jack